Access to gem-Dibromoenones Enabled by Carbon-Centered Radical Addition to Terminal Alkynes in Water Solution

Xianghua Zeng*, Yuhai Xu, Jiawei Liu and Yuanyuan Deng

*College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P.R. China, Email: xianghuazengzjxu.edu.cn

X. Zeng, Y. Xu, J. Liu, Y. Deng, Org. Lett., 2021, 23, 9058-9062.

DOI: 10.1021/acs.orglett.1c03305

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Abstract

The generation of a tribromomethyl radical from tetrabromomethane (CBr₄) with the assistance of a persulfate salt (K₂S₂O₈) enables a single step conversion of terminal alkynes to gem-dibromoenones in the presence of water. The reaction features readily available chemicals, a broad substrate scope, a green solvent, and mild reaction conditions.

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proposed mechanism

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Key Words

dihaloalkenes, enones, potassium peroxydisulfate

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ID: J54-Y2021